50995-74-9Relevant academic research and scientific papers
Constructing Cross-Linked Nanofibrous Scaffold via Dual-Enzyme-Instructed Hierarchical Assembly
Cortes, William,Zhang, Shijin,Zhang, Ye
, p. 6261 - 6267 (2020)
To explore the potential of step-by-step assembly in the fabrication of biological materials, we designed and synthesized two peptide-based molecules for enzyme-instructed hierarchical assembly. Upon the treatment of alkaline phosphatase, one molecule undergoes enzyme-instructed self-assembly forming uniformed nanofibers. The other one that can self-assemble into vesicles undergoes enzyme-induced transformation of self-assembly converting vesicles into irregular aggregates upon the treatment of carboxylesterase. Coadministration of two enzymes to a mixture of these two molecules in a stage-by-stage fashion leads to a physically knotted nanofibrous scaffold that is applicable as a nanostructured matrix for cell culture.
A New Fluorescent “Turn-Off” Coumarin-Based Chemosensor: Synthesis, Structure and Cu-Selective Fluorescent Sensing in Water Samples
Karaoglu, Kaan,Yilmaz, Fatih,Mente?e, Emre
, p. 1293 - 1298 (2017)
We report the synthesis and characterization two coumarin-based fluorescence probes, N′-{[7-(diethylamino)-2-oxo-2H-chromen-3-yl]carbonyl}pyridine-3-carbohydrazide (3) and N′-benzoyl-7-(diethylamino)-2-oxo-2H-chromene-3-carbohydrazide (4), proposed as a novel fluorescent chemosensor. The two probes designed showed an instant turn-off fluorescence response to Cu2+ over other metal ions in ethanol-water mixture based on intramolecular charge transfer (ICT). It was found that pyridine-analogue coumarin is highly selective and sensitive sensor for Cu2+. The 3 sensor coordinates Cu2+ in 1:1 stoichiometry with a binding constant, Ka?=?5.22?M?1 and the detection limit was calculated 1.97?×?10?9?M.
Selective and ratiometric fluorescent trapping and quantification of protein vicinal dithiols and in situ dynamic tracing in living cells
Huang, Chusen,Jia, Ti,Tang, Mengfang,Yin, Qin,Zhu, Weiping,Zhang, Chao,Yang, Yi,Jia, Nengqin,Xu, Yufang,Qian, Xuhong
, p. 14237 - 14244 (2014)
Protein vicinal dithiols play fundamental roles in intracellular redox homeostasis due to their involvement in protein synthesis and function through the reversible vicinal dithiol oxidation to disulfide. To provide quantitative information about the glob
A highly sensitive fluorescent probe for selective detection of Al3+ cation by switching the solvent from aprotic to protic environment
Park, Junemin,Angupillai, Satheshkumar,Son, Young-A.
, p. 103 - 113 (2015)
We have designed and synthesized known coumarin-rhodamine (CR1) derivative for sensing the Al3+ ion in the presence of aprotic (CH3CN/H2O) medium via TBET mechanism. The results of the photo physical studies revealed that the sensing mechanism involves Al3+ induced change from non-fluoroscent (spirolactam form) to fluorescent (ring opening form) in CR1 leading to the visible color change. The Job's plot indicated the formation of 2:1 complex between CR1 and Al3+ with limit of detection is 1.78 × 10-8 M. Various spectroscopy techniques and theoretical calculation have been employed to investigate the mechanism of the sensing property of CR1 with Al3+.
Anti-hypochlorite, antioxidant, and catalytic activity of three polyphenol-rich super-foods investigated with the use of coumarin-based sensors
Starzak, Karolina,?wiergosz, Tomasz,Matwijczuk, Arkadiusz,Creaven, Bernadette,Podle?ny, Janusz,Karcz, Dariusz
, (2020)
The anti-hypochlorite activity of a?aí (Euterpe oleracea Mart.), goji (Lycium barbarum L.) and schisandra (Schisandra chinensis) fruit extracts were assessed by determining the reactive chlorine species (RCS)-scavenging ability of these three “super-food” berries. In addition, the aqueous extracts obtained were employed as both the media and the catalyst in a green chemistry approach to the synthesis of a coumarin-based fluorescence turn-off sensor, which was then used for anti-hypochlorite activity testing. The aqueous extracts were also assessed for total phenolic content (TPC), using the Folin–Ciocalteu method, and the antioxidant activity using the ABTS+? assay. Moreover, the main water-soluble polyphenolic constituents of the extracts were identified by the HPLC-PDA-ESI-MS technique. Among the extracts tested, a?aí demonstrated the highest anti-hypochlorite and antioxidant activities, while the highest TPC value was found for the goji extract. All extracts demonstrated modest catalytic activity as Knoevenagel condensation catalysts.
Highly promising discrimination of various catecholamines using ratiometric fluorescence probes with intermolecular self-association of two sensing elements
Sanguansap, Yanisa,Ruangpornvisuti, Vithaya,Tuntulani, Thawatchai,Promarak, Vinich,Tomapatanaget, Boosayarat
, p. 78468 - 78475 (2015)
Two sensing elements based on fluorescence probes have been employed as the promising discriminating sensors of two catecholamines, dopamine (DA) and norepinephrine (NE), acting as a proper guest linker between two self-recognition sensing components. Surprisingly, in the presence of epinephrine (EPI), sensor NB containing boronic acid connected to a napthalimide unit demonstrated a very strong fluorescence enhancement while a large fluorescence quenching was observed in the case of DA and NE. To differentiate the structural similarity of DA and NE, an appropriately designed small fluorescence sensor CC containing a crown-ether attached to coumarin showed complementary recognition to an ammonium ion based catecholamine. The combination of NB and CC is capable of the differentiation of DA and NE with dual emission bands under a PET mechanism. The dual emission ratio (I475/I384) of the NB-DA-CC complex showed different values from those of the NB-NE-CC complex. Additionally, the PCA analysis using mixed sensors of NB and CC obviously separated DA and NE better than a single sensing element. This systematic approach is the first report showing a high potential for the identification of DA and NE using ratiometric fluorescence sensors with dual emission by two sensing elements.
A water soluble fluorescent polymer as a dual colour sensor for temperature and a specific protein
Inal, Sahika,Koelsch, Jonas D.,Sellrie, Frank,Schenk, Joerg A.,Wischerhoff, Erik,Laschewsky, Andre,Neher, Dieter
, p. 6373 - 6381 (2013)
We present two thermoresponsive water soluble copolymers prepared via free radical statistical copolymerization of N-isopropylacrylamide (NIPAm) and of oligo(ethylene glycol) methacrylates (OEGMAs), respectively, with a solvatochromic 7-(diethylamino)-3-carboxy-coumarin (DEAC)-functionalized monomer. In aqueous solutions, the NIPAm-based copolymer exhibits characteristic changes in its fluorescence profile in response to a change in solution temperature as well as to the presence of a specific protein, namely an anti-DEAC antibody. This polymer emits only weakly at low temperatures, but exhibits a marked fluorescence enhancement accompanied by a change in its emission colour when heated above its cloud point. Such drastic changes in the fluorescence and absorbance spectra are observed also upon injection of the anti-DEAC antibody, attributed to the specific binding of the antibody to DEAC moieties. Importantly, protein binding occurs exclusively when the polymer is in the well hydrated state below the cloud point, enabling a temperature control on the molecular recognition event. On the other hand, heating of the polymer-antibody complexes releases a fraction of the bound antibody. In the presence of the DEAC-functionalized monomer in this mixture, the released antibody competitively binds to the monomer and the antibody-free chains of the polymer undergo a more effective collapse and inter-aggregation. In contrast, the emission properties of the OEGMA-based analogous copolymer are rather insensitive to the thermally induced phase transition or to antibody binding. These opposite behaviours underline the need for a carefully tailored molecular design of responsive polymers aimed at specific applications, such as biosensing.
A coumarin Schiff's base two-photon fluorescent probe for hypochlorite in living cells and zebrafish
Wang, Kangnan,Sun, Pengzhen,Chao, Xijuan,Cao, Duxia,Mao, Zongwan,Liu, Zhiqiang
, p. 6904 - 6909 (2018)
Selective and sensitive fluorescent probes for ClO- are desirable due to the importance of ClO- in biological processes. Here, a coumarin Schiff's base, compound 1, has been developed and successfully used as a one- and two-photon fluorescent probe for ClO- with high selectivity. This probe can recognize ClO- with obvious color change from yellow-green to colorless and green to blue fluorescence emission, which can be observed by the naked eye. The properties of low cytotoxicity and good cell permeability allow it to be used for ClO- detection in living cells and zebrafish by both one- and two-photon microscopy imaging. All these results indicate that the compound is a sensitive probe with potential for analysis of ClO- in biological samples. The mechanism by which probe 1 recognizes ClO- is possibly nucleophilic addition followed by hydrolysis.
A novel ratiometric probe based on rhodamine B and coumarin for selective recognition of Fe(III) in aqueous solution
Ge, Fei,Ye, Hui,Zhang, He,Zhao, Bao-Xiang
, p. 661 - 665 (2013)
We have developed a new ratiometric fluorescence probe based on rhodamine B and coumarin to monitor the Fe3+ with high sensitivity and selectivity. Upon addition of Fe3+ to aqueous solution of the probe, two fluorescence peaks at 580 nm and 460 nm were observed, which belong to rhodamine B and coumarin, respectively. This is a novelty design of ratiometric probe of Fe3+, due to CHEF process generated along with the PET process suppressed simultaneously. The fluorescence intensity at 580 nm was significantly increased about 120-fold with 5 equiv. of Fe3+ added in aqueous solution.
General Strategy for in Situ Generation of a Coumarin-Cu2+ Complex for Fluorescent Water Sensing
Cheng, Wenjing,Xie, Yiting,Yang, Zhiyu,Sun, Yueqing,Zhang, Ming-Zhi,Ding, Yubin,Zhang, Weihua
, p. 5817 - 5823 (2019)
The detection of moisture in organic solvents is very important before their use in water-sensitive reactions. Herein, we report that coumarins D1 and D2 were able to generate the corresponding water-sensitive copper complexes D1-Cu and D2-Cu in common organic solvents, which can be used as efficient fluorescent turn-on sensors for water. Single-crystal diffraction analysis of the reaction product indicated that the sensing mechanism is based on the formation of a water-bridged 3D supramolecular hydrogen-bonding network. We demonstrated that a hydroxyl or amine group substituted at the 7-position of the coumarin framework played a key role in the water-sensing performance of D1-Cu and D2-Cu, by acting as a hydrogen bond acceptor in the supramolecular network. This provided a general strategy for designing such coumarin-based copper complexes for fluorescent water sensing. The water-sensing behavior of D1-Cu and D2-Cu were determined to be fast, pH tolerant, and sensitive. As low as 0.0525 wt % of water in methanol can be detected using D1-Cu as the sensor. Moreover, D1-Cu was successfully used for moisture sensing in real commercial products.
